Gabapentin [1-(aminomethyl)cyclohexaneacetic acid, C9H17NO2] is a zwitterio
n in the solid state. Its crystal structure involves extensive hydrogen bon
ding between the NH3+ and COO- groups of neighboring molecules. The structu
re of gabapentin monohydrate [1-(aminomethyl)cyclohexaneacetic acid monohyd
rate, C9H17NO2.H2O] also involves such hydrogen bonding and, in addition, h
as a hydrogen-bonding network comprising the water molecules and both the N
H3+ and COO- groups.